Reaction equation
Cl.CN(C)CCCN=C=NCC.[Cl:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22].[O:23]1[CH2:27][CH2:26][CH2:25][CH:24]1[C:28](O)=[O:29].O>ClCCl.CN(C)C1C=CN=CC=1>[O:23]1[CH2:27][CH2:26][CH2:25][CH:24]1[C:28]([O:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][Cl:13])=[O:29]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (5.7 g) in dichloromethane (100 ml) was slowly added to a solution of 8-chloro-1-octanol (4.1 g), tetrahydro-2-furancarboxylic acid (3.5 g) and 4-dimethylaminopyridine (1.5 g) in dichloromethane (50 ml) at 0° C. The mixture was stirred overnight at room temperature. The resulting solution was then added to water (500 ml) and extracted with dichloromethane (3×200 ml). The combined organic layers were washed with water (2×200 ml), dried over magnesium sulphate and filtered. The solvent removed in vacuum. The residue (7 g) was purified by column flash chromatography on silica gel using toluene/ethyl acetate (90:10) as eluent to give 8-chlorooctyl tetrahydro-2-furancarboxylate.
Workup
- extractionextracted with dichloromethane (3×200 ml)
- washThe combined organic layers were washed with water (2×200 ml)
- dry with materialdried over magnesium sulphate
- filtrationfiltered
- customThe solvent removed in vacuum
- customThe residue (7 g) was purified by column flash chromatography on silica gel
Sources & evidence
- ORD record
- ord-aeed6a2dc3f048fcbafc995ea6a74d98
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08105662B2
Linked notes
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